$3,100,000
Off-Market Date: 06/27/2026321 Lookout Point Drive Osprey, FL 34229
Pending MLS# A4697345
3 beds 4 baths 3,122 sq ft Single Family
Details for 321 Lookout Point Drive
MLS# A4697345
Description for 321 Lookout Point Drive, Osprey, FL, 34229
Experience the epitome of waterfront living in the sought-after Southbay neighborhood. This 3 bedroom, 3.5 bath home is ideally positioned on a peninsula, providing sweeping panoramic water views. The moment you step inside, you will be mesmerized by the breathtaking bay views through a plethora of windows and sliding glass doors that flood the space with natural light. The open, main level is designed for both comfort and style, with vaulted ceilings, unobstructed water views from every room and hardwood floors. The kitchen is uniquely designed, featuring an extended breakfast bar, high end designer cabinets and stainless steel appliances. The great room, with wet bar, has views so perfect, they almost feel like artwork. The new clear view lanai screens provide a gorgeous tropical back drop to the pool and spa. Host friends and loved ones, using the outdoor kitchen and setting area for a fun-filled dinner, and watch the sun set, painting the sky with a golden glow. The first floor master suite consists of a spacious bedroom, a spa-like bathroom, and a separate area utilized as a private study. Upstairs you will find two additional en suite bedrooms. One opens to the new deck, has views over the Dryman Bay out to Casey Key, and is large enough to use as a second master suite. While the views and location of this home are drop-dead gorgeous, practical features also abound. This home has impact windows and doors, a brand new washer and dryer, and recently replaced roof, AC and tankless hot water heater. Southbay Yacht and Racquet Club has a seven-acre deep-water marina accommodating boats up to 55 feet with slips available to homeowners. It has an updated clubhouse and fitness center overlooking the bay, complete with a ballroom, catering kitchen, meeting room and library. Community amenities also include a geothermal heated pool, children’s pool, tennis, pickleball, shuffleboard, basketball and kayak storage. Residents enjoy 20 acres of lush common grounds and five miles of walking trails, plus a vibrant calendar of social events.
Listing Information
Property Type: Residential, Single Family Residence
Status: Pending
Bedrooms: 3
Bathrooms: 4
Lot Size: 0.34 Acres
Square Feet: 3,122 sq ft
Year Built: 1978
Garage: Yes
Stories: 2 Story
Construction: Stucco
Subdivision: Southbay Yacht & Racquet Club
Foundation: Slab
County: Sarasota
School Information
Elementary: Laurel Nokomis Elementary
Middle: Sarasota Middle
High: Venice Senior High
Room Information
Main Floor
Porch: 29x48
Primary Bedroom: 13x19
Kitchen: 12x19
Dining Room: 13x21
Great Room: 20x34
Upper Floor
Bedroom 3: 13x16
Bedroom 2: 13x14
Bathrooms
Full Baths: 3
1/2 Baths: 1
Additonal Room Information
Laundry: Inside
Interior Features
Appliances: Built-In Oven, Cooktop, Dishwasher
Flooring: Carpet,Tile,Wood
Additional Interior Features: High Ceilings
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Electricity Connected
Cooling: Central Air
Heating: Central
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 2
Roof: Tile
Pool: In Ground
Additional Exterior/Lot Features: Outdoor Grill, Outdoor Kitchen, Balcony, Balcony
Community Features
Homeowners Association: Yes
HOA Dues: $657 / Quarterly
Driving Directions
Rte. 41/South Tamiami Trail to Blackburn Point Rd. West on Blackburn. Make a right on Southbay Drive. Make a left on Harbor Huse Drive. Make a right on Lookout Point Dr. to address.
Financial Considerations
Terms: Cash,Conventional
Tax/Property ID: 0158020018
Tax Amount: 16001.71
Tax Year: 2025
A broker reciprocity listing courtesy: COLDWELL BANKER REALTY
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Copyright 2026 Stellar MLS as distributed by the MLS GRID. All Rights Reserved.
Sales History & Tax Summary for 321 Lookout Point Drive
Sales History
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Tax Summary
| Tax Year | Estimated Market Value | Total Tax |
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
Schools
Schools nearby 321 Lookout Point Drive
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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